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Biologically active glycosides from asteroidea, XIX. Glycosphingolipids from the starfish Acanthaster planci 4. Isolation and structure of five new gangliosides
Author(s) -
Kawano Yasuhiro,
Higuchi Ryuichi,
Komori Tetsuya
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900107
Subject(s) - chemistry , starfish , acanthaster , hydrolysis , oligosaccharide , moiety , chloroform , chromatography , organic chemistry , biochemistry , ecology , oceanography , great barrier reef , coral reef , biology , geology
Five new gangliosides — acanthaganglioside A ( 1 ), B ( 2 ), C ( 3 ), D ( 4 ) and E ( 5 ) — were purified from the water‐soluble lipid fraction of the chloroform/methanol extract of the starfish Acanthaster planci. Based on chemical and spectroscopic data, the structures of 1 – 5 were elucidated. The gangliosides consist of one homogeneous long‐chain base, five or six sugars and different fatty acids. Reversed‐phase HPLC using methanol/ammonia/water as solvent was effective in isolating these gangliosides, showing the very close similarity in their structures. Negative FAB mass spectrometry provided important information both on the structure of the sugar moiety and on the molecular mass of the gangliosides. Partial hydrolysis by hot pyridine/water or hot water was useful for structure elucidation of the complex oligosaccharide moieties.